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Caribbean vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Caribbean

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Villa in Las Terrenas
Villa WOW: 1 million dollar ocean view + sunset
A spectacular WoW villa, in the mountains, overlooking Playa Coson. ***This is NOT a party villa. We have neighbors here. In the daytime low-level music and after 10 pm NO Music. A very spacious and comfortable, private villa, with all comfort. And a huge pool, a swim-up bar, and an infinity pool. The villa is 8 minutes distance from center of town, where you will have shopping facilities, restaurants, and bars. In the mountains. 4x4 car is advised. Electricity NOT included.
$257 per night
Villa in Punta Cana
Villa Jazmines & SPA Jacuzzi- Punta Cana Village
Villa Jasmines is a luxury home, decorated with a tropical theme, perfect place for accommodation and pleasant rest in Punta Cana Village. Located in a private community (24 h. security) & walking distance from supermarket, shopping, parks, playground, tennis courts, restaurants and just few min drive from the airport, 5 min drive to the golf course, luxury beach clubs with bars, and Ecological Reserve with natural lagoons. Within 10 min from the famous Coco Bongo Show and Disco!
$219 per night
Condo in Collectivity of Saint Martin
Paradise vacation on La Plage
Apartment with magnificent sea views Directly on Nettlé Bay beach with pool Close to shops Restaurant, bakery, pharmacy... 15 minutes from Juliana International Airport and Mullet Bay Golf Plage de Baie rouge et baie aux prunes 10 Minutes Although life on our Friendly island is very good , it is to be noted that electricity and water disruptions may happen please be assured that all concerned do their utmost to minimize any Inconvénience «  Thank You 🥰
$145 per night

Caribbean beach vacation rentals

Cabin in Culebra
Flamenco Toe - Glamping
$425 per night
Rental unit in Aguadilla Pueblo
Oasis- bottom balcony ocean view + modern
$174 per night
Villa in San Nicolas
BeachFront Villa w/ Pool, Sleeps 16, Dining, & Tub
$918 per night
Guest suite in Ocho Rios
Luxury White Sand Beach Cottage 1 bd with Chef
$295 per night
Home in Isabela
Oceanfront Hideaway Main Floor
$164 per night
Villa in Río Grande
Villa Morivivi / Beach Front
$455 per night
Private room in Cruz Bay
Hawk's Rest
$135 per night
Tiny home in Sarasota
Tiny House Green Lifeguard Stand located 3/4 of a mile from the beach in our Tin
$138 per night
Condo in Miami
Waterfront Spacious Luxury 1 Bedroom IconBrickell
$175 per night
Condo in Río Grande
Spacious Villa @ Rio Mar, Rio Grande/ Sleeps 6
$124 per night
Condo in Naples
Couples Hideaway Short Walk to Beach
$189 per night
Bungalow in Grace Bay
Grace Shore Villas Cottonflower
$396 per night

Luxury vacation rentals in Caribbean

Home in North Side
Ocean's Edge: Beachfront Home with Rooftop Views
$550 per night
Villa in Les Terres Basses
$714 per night
Villa in Isabela
🌴Isabela Retreat Over looking Golf Course & Ocean
$818 per night
Home in Punta Rucia
Villa Mare - Ocean Front
$809 per night
Home in Las Terrenas
Amazing sea view luxury modern, fully staffed
$596 per night
Villa in Galina
*Luxury Rental* The Palms at Galina
$775 per night
Villa in Les Terres Basses
Terrasse De Mer
$957 per night
Home in Hallandale Beach
Luxury Home on The Water 5BD
$803 per night
Villa in Miami
Brand new Villa for 14 ! Pool / PING PONG
$993 per night
Home in Grand Cayman
Lone Palm by Grand Cayman Villas
$840 per night
Villa in Isabela
Isabela Retreat Over looking Golf Course & Ocean
$625 per night
Villa in Treasure Beach
Shakti Home- The villa you've been dreaming about!
$607 per night

Caribbean winter vacation rentals

Tent in Miramar
$132 per night
Tiny home in Rincon
Casa Valentina
$174 per night
Home in Delray Beach
Dream Tropical Pool House Delray Beach near Ocean
$280 per night
Tiny home in Aguada
Aguada Secret Spot
$112 per night
Home in Adjuntas
💚Hidden Gem w/Chimney, Jacuzzi & Heated Pool💚
$475 per night
Condo in Carolina
"Heart of the Island" ❤️ "Corazon de la Isla"
$185 per night
Villa in St. John
Penthouse & Gorgeous View in St John Paradise
$319 per night
Home in Aguadilla Pueblo
Villa Flamboyan
$1,000 per night
Vacation home in Jobos, Isabela
$95 per night
Tent in Tajo Alto
$115 per night
Cabin in La fortuna
Arenal Love Cabin, Lake & volcano view.
$132 per night
Place to stay in Punta Cana
Hut #3 Romantic Luxury on the sand
$109 per night

Your guide to Caribbean

All About the Caribbean

The Caribbean is made up of 26 island countries surrounded by bejeweled blue and green waters and is known around the world as a holiday paradise. People flock here, especially in the winter, for warm sands, golden sunshine, and that sense of island time abandon — plus, the fruity drinks under towering palm trees. The Dominican Republic is the most visited of all the islands due to its vibrant city and cultural life and postcard-perfect beaches. West of that is Cuba, famous for its Old World architecture, rich jazz and music scenes, and several UNESCO World Heritage Sites. Closer to South America is little St. Lucia, known for its rainforests, colorful coral reefs (perfect for diving and snorkeling), and, of course, pristine beaches surrounded by the island’s volcanic peaks.

The countries in the Caribbean are extremely diverse, not only in their histories, cultures, and languages, but their landscapes and topographies. For example, vibrant Jamaica could not be more different from super-chill Aruba and swanky St. Barts. So whether you’re seeking an island that’s large or small, glitzy or low-key, in the Caribbean there is a sanctuary for everyone.

When is the best time to stay in a vacation rental in Caribbean?

Thanks to trade winds, the weather in the Caribbean is sunny and pleasant all year round. The only caveat is that tropical storms and hurricanes occur to varying degrees of intensity here, and their likelihood increases from about July to November. But it’s the dry season from December through March that makes the region so popular. Villas to rent in the Caribbean are in demand during the winter, as many feel the urge to escape the colder weather up north and take in the sun, fun, and the many festivals — like Trinidad’s Carnival, the biggest of the Caribbean’s carnivals, and the Bahamas’ Junkanoo, a cultural street festival and celebration dating back centuries that takes place between Boxing and New Year’s Day. There are also plenty of Caribbean rentals in May and June, if you don’t mind the chance of a little rain.

What are the top things to do in Caribbean?

Santo Domingo

Santo Domingo, the capital of the Dominican Republic, is the oldest continuously inhabited colonial settlement in the Western Hemisphere and was founded in 1496. The historic city center, Zona Colonial, is a UNESCO World Heritage Site, with cobblestone streets, colorful houses, and colonial-style architecture and structures like the 16th-century Basilica Cathedral of Santa María la Menor, the oldest surviving cathedral in the Americas.


Sitting off the coast of Venezuela is the Dutch island of Curaçao, lesser known than its neighbors, but with just as much to offer — including its lack of hurricane seasons. Willemstad, the capital, is one of the few UNESCO World Heritage cities in the Caribbean, and it’s pulsing with nightlife and festivals like Carnival and King’s Day. The diving here is top-notch, there are dozens of stunning beaches to choose from, and the lodging ranges from hostels to five-star resorts — so there’s something here for everyone.

Reggae in Jamaica

Jamaica is the birthplace of reggae. The music took off in the late 1960s, and by the 1970s, with the superstardom of Bob Marley and the Wailers, it became known throughout the world. If you’re in Kingston, check out the clubs, still playing the dub style that made the genre so popular. The best of the best musicians have been known to play at the annual reggae festival held in June.